反应详情

温度

95 °C

2-((2-Chloro-4-(dimethylcarbamoyl)phenyl)(methyl)carbamoyl)-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-8-carboxylic acid (0.15 g, 0.31 mmol) was dissolved in SOCl2 (10 mL). The solution was heated at 90-100° C. for 3 hours. Removal of the rest SOCl2 gave the crude product. A solution of the crude acid chloride in THF (12 mL) was treated with a solution of ethanamine (0.14 g, 3.1 mmol) and Pyridine (0.3 mL) in THF (8 mL) at 0° C. The reaction mixture was allowed to reach room temperature and stirred overnight. Concentrated to remove THF to afford the crude product, it was purified by preparative TLC to obtain 347 (48.5 mg, 31%). ESI-MS: 512. 1H NMR (CDCl3, 400 MHz): δ7.59 (s, 1H, ArH), 7.44-7.32 (m, 5H, ArH), 6.95 (s, 1H, ═CH), 6.12 (s, 1H, NH), 4.23 (t, J=5.0 Hz, 2H, CH2), 3.51-3.44 (m, 2H, CH2), 3.39 (s, 3H, CH3), 3.13 (s, 3H, CH3), 3.05 (t, J=5.0 Hz, 2H, CH2), 3.02 (s, 3H, CH3), 1.24 (t, J=7.2 Hz, 3H, CH3).

1. customRemoval of the rest SOCl2
2. customgave the crude product
3. customto reach room temperature
4. concentrationConcentrated
5. customto remove THF
6. customto afford the crude product, it
7. customwas purified by preparative TLC